Diisobutylaluminumhydride → HCID 21256464, compound

HRID 635882Notes

Reaction equation

HRID 635882 reaction equation
[CH3:1][C:2]1[S:6][C:5]2=[N:7][CH:8]=[C:9]([C:10](=[O:20])[CH2:11][CH:12]([OH:19])[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:4]2[C:3]=1[CH3:21].[H-].C([Al+]CC(C)C)C(C)C>C1(C)C=CC=CC=1>[CH3:1][C:2]1[S:6][C:5]2=[N:7][CH:8]=[C:9]([CH:10]([OH:20])[CH2:11][CH:12]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[OH:19])[N:4]2[C:3]=1[CH3:21]

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 21256478HCID 21256478, compound

Product 1

HCID 21256464HCID 21256464, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1-(2,3-Dimethylimidazo[2,1-b]thiazol-5-yl)-3-hydroxy-3-phenyl-1-propanone (Formula R-3, X=H), 0.08 g, in toluene (10 mL) was treated with 1M diisobutylaluminum hydride (1.0 mL) and reacted for 1.25 hours. The solution was quenched into 5% citric acid, the mixture was extracted with ethyl acetate and the citric acid solution was neutralized with NaOH. Extraction of product from the neutralized solution gave pure 1-(2,3-Dimethylimidazo[2,1-b]thiazol-5-yl)-3-phenyl-1,3-propanediol (Formula R-4, X=H), 0.04 g, m.p. 152-153° after crystallization from CH2Cl2/CH3CN solution.

Workup

  1. customreacted for 1.25 hours
  2. customThe solution was quenched into 5% citric acid
  3. extractionthe mixture was extracted with ethyl acetate
  4. extractionExtraction of product from the neutralized solution

Sources & evidence

ORD record
ord-6a217e04d14b4df0b4a9386bc1e2b0cc
Source dataset
uspto-grants-2001_02
Patent number
US06191124B1

Reaction notes

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